How do you look ahead into the calendar a few weeks? I could only go a few days ahead by swiping events before it stopped letting me, and I'm not able to click on the date number in a few weeks, it doesn't let me.
If you click on the little arrow to the left of 'Today' (or whatever date it's on at the moment) you can see a monthly calendar for the current month, but it only shows the dates. You can't see any actual appts or anything like that for a date more than 1 week in the future.
Its a limitation / design decision of Apple calendar app. Technically the maximum events window in EventKit is like 4 years and then you can shift it back and forth so pretty much endless but the app has to deal with all the data and processing required which isnt best suited for the Watch. Have a look at 3rd party calendar apps like Fantastical etc, some of them might offer larger events window.